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D-(-)-PANTOLACTONE

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CAS:599-04-2
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D-(-)-PANTOLACTONE Basic information
Product Name:D-(-)-PANTOLACTONE
Synonyms:(R)-()-β,β-Dimethyl-α-hydroxy-γ-butyrolactone;(R)-(-)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE;(R)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE;(R)-(-)-BETA,BETA-DIMETHYL-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE;(R)-(-)-ALPHA-HYDROXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE;R(-)-3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE;R(-)-2-HYDROXY-3,3-DIMETHYL-GAMMA-BUTYROLACTONE;PANTOIC ACID GAMMA-LACTONE
CAS:599-04-2
MF:C6H10O3
MW:130.14
EINECS:209-963-3
Product Categories:Pharmaceutical Intermediates;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:599-04-2.mol
D-(-)-PANTOLACTONE Structure
D-(-)-PANTOLACTONE Chemical Properties
Melting point 91 °C(lit.)
Boiling point 120-122 °C15 mm Hg(lit.)
density 1.1066 (rough estimate)
vapor pressure 0.3-3.28Pa at 15-35℃
refractive index -50.8 ° (C=2, H2O)
Fp 120-122°C/15mm
storage temp. 2-8°C
solubility Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)
pKa13.12±0.40(Predicted)
form Crystals or Crystalline Powder
color White
Odorcotton candy
Optical Rotation[α]25/D 49.8°, c = 2 in H2O
Water Solubility almost transparency
Sensitive Hygroscopic
Merck 14,7013
BRN 80957
Major Applicationpharmaceutical (small molecule)
Cosmetics Ingredients FunctionsHUMECTANT
SKIN CONDITIONING
InChI1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
InChIKeySERHXTVXHNVDKA-BYPYZUCNSA-N
SMILESCC1(C)COC(=O)[C@@H]1O
LogP-0.973--0.46 at 22.5-25℃ and pH7.1
CAS DataBase Reference599-04-2(CAS DataBase Reference)
EPA Substance Registry SystemPantolactone (599-04-2)
Safety Information
Safety Statements 22-24/25
WGK Germany 1
3-10
TSCA TSCA listed
HS Code 29322090
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
D-(-)-PANTOLACTONE Usage And Synthesis
Chemical PropertiesWHITE CRYSTALLINE POWDER OR CRYSTALS
UsesD-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.
It can be used as a chiral starting material to synthesize:
  • An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.
  • (-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.
  • A bicyclic diterpene named isofregenedadiol.

UsesD-(-)-PANTOLACTONE is an important intermediate in the synthesis of pantothenic acid as well as a degradation product of pantothneic acid in the liver. Causes disorientation and hypothermia, and prevents phenamine-induced hyperthermia.
DefinitionChEBI: (R)-pantolactone is a butan-4-olide that is dihydrofuran-2(3H)-one substituted by a hydroxy group at position 3 and two methyl groups at position 4 (the R-stereoisomer). It has a role as a Saccharomyces cerevisiae metabolite. It is functionally related to a (R)-pantoic acid.
General DescriptionPharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Purification MethodsRecrystallise the lactone from Et2O/pet ether, diisopropyl ether or *C6H6/pet ether and sublime it at 25o/0.0001mm. It hydrolyses readily to the hydroxy-acid and racemises when heated above 145o. The Brucine salt has m 211-212o (from EtOH). [Kuhn & Wieland Chem Ber 73 1134 1940, and Stiller et al. J Am Chem Soc 62 1779 1940, Bental & Tishler J Am Chem Soc 68 1463 1946, Beilstein 18/1 V 22.]
D-(-)-PANTOLACTONE Preparation Products And Raw materials
Raw materialsMethanol-->Sulfuric acid-->Formaldehyde-->Sodium cyanide-->Isobutyraldehyde-->HYDROGEN CYANIDE
Preparation ProductsSodium D-pantothenate-->Calcium D-Pantothenate
Tag:D-(-)-PANTOLACTONE(599-04-2) Related Product Information
H-BETA-ALA-BETA-ALA-OH (2S)-2,4-Dihydroxy-3,3-dimethylbutanoic acid (R)-Methyl 3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate Vitamin B5 Impurity 1 3,3-BIS(N,N-DIPROPANOIC ACID) DL-Pantolactone PICROTOXIN L-Pantolactone, (S)-(+)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone,(S)-(+)-PANTOLACTONE,L-PANTOLACTONE ALPHA-HYDROXY-GAMMA-BUTYROLACTONE Bilobalide GINKGOLIDEM Ginkgolide A Ginkgolide J PICROTOXININ Ginkgolide B Ginkgolide C PICROTIN Gamma Butyrolactone

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